Where does your yearly spend go?

We often get asked what's included in your yearly spend.  The answer is largely the same for our Cloud and Locally hosted customers when it comes to product enhancements, access to Customer Care and Advanced User Training such as Windward Webinars and the Windward Learning Academy.  Our cloud customers enjoy some added benefits which are listed in the section for Cloud Subscriptions below.

Why settle for an outdated version of your business management solution, Windward System Five, when you can experience the most recent, most powerful solution?  Secure the future of your business by renewing your maintenance plan today! Call your account manager at (800) 663-5750

Keep scrolling for details regarding Windward System Five Enhancements, Customer Care, User Education and Training and Cloud Subscriptions.

Maintenance Plan


  • Windward System Five Enhancements
  • 24/7 Access to Customer Care
  • User Education and Training
  • And more
What People Are Saying
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Windward System Five Enhancements
Windward System Five

Custom Modifications, if beneficial for a wider audience, usually
make their way into General Releases. If an enhancement requires a work-flow consultation, Professional Services are available for a charge. Most functionality listed is part of your product updates, with the exception of Integrations and Major Modules. 

Prioritized by customer impact, we assure full-time resources are dedicated to fixes of System Five. While defects are an inevitable part of software development, the best way to prevent them is to find them pre-release. We have multiple QA staff who test functionality and use regression testing to help automate and enhance our Quality Assurance Testing processes.

We have recently undergone extensive training and certification with Microsoft directly. We are now certified Gold for Application Development, Silver for Data Analytics, and Gold for Cloud Platform, which means we build solutions to work best with the standard business tools you already use today. Check this link to see the certifications we've obtained.

Microsoft Gold And Silver Partner

For those who opt to use integrated credit and debit card processing, there is a substantial verification process required for software vendors to assure certification. Windward Software has maintained PCI certification, this focus on the protection of information and safeguarding data is absolutely paramount.

Make sure you understand your part in being PCI Compliant by clicking here.

24/7 Access to Customer Care

We maintain a 24/7 Support schedule

We maintain a 24/7 Support schedule, balancing the resources based on the volume of inbound activity. Note that we have moved some activities such as installs and product updates to be scheduled outside of North American business hours. This helps us be available when you need us.  

Connect with customer care using the below methods:

By Phone

Best for urgent tickets 

Our "First Responder" initiative assures that the majority of tickets are resolved on the first call.

Dial +1(800) 663-5750

By Email

Suitable for less urgent inquiries

Specifically useful when screen shots and additional context is required

click here to launch an email to support@windwardsoftware.com


Customer Care Portal

Search our Knowledge Base

Request Support

Track ticket progress


Access to Training Dataset

One tool we find is under-utilized (at least past Go-Live) is the use of a training dataset. Having access to a 'sandbox' version of your system is very important for testing work-flow changes, new functionality, and validating updates before you put them into Production. Give your new employees access to the training area to the work-flow for their role. 

Email support@windwardsoftware.com to copy over your dataset to training.

Management of Supported Hardware

Understanding what devices and accessories are supported with Windward System Five is important for you to get the best return on your software investment. If you aren't currently utilizing barcode scanners, cash-drawers, or other peripherals that would help in practical deployment, please see the provided link.

Supported Hardware and Peripheral List

Escalation to Programmer

If there is an incident the Customer Care team can’t figure out, we offer consultation with the programming team.

Windward Education and Training
Windward Webinars

Windward Webinars

Our Webinar schedule, which focuses on various product and workflow topics, are held bi-weekly.

Available only for customers on Maintenance or Subscriptions (On-Cloud).

Windward Learning Academy

This online learning platform is available to help you and your staff learn the software. The Academy has topic and role-based learning plans that include quizzes to engage your staff in the learning process.

Login to the Academy

Searchable Self Help

Quick Reference guide that has been indexed for easy access to your questions.  Available for when you need a quick answer.

Access Searchable Self Help

Windward Professional Services

Consultative Professional Services are also available for advanced training that is not included in Maintenance: 

Windward Cloud Subscriptions

System Five on Cloud Subscriptions

System Five on Cloud includes all of the above and then some.  Windward has moved to Windows Virtual Desktop Services, managed by Microsoft in Azure.  Our cloud subscribers get Automated Windows Updates, Automated Backups, Multi-Factor Authentication, and Dedicated Security Personnel who consult with industry-leading cybersecurity experts.  

A subset of our cloud subscribers is the first to get new features deployed and is on the fast track to the native cloud.  Some have even been selected for and have volunteered to get involved with our SQL Preview.

System Five on Cloud

Take me to the Cloud info Page

Windward Intelligence

Windward Intelligence

Windward Intelligence is a Sales Analysis tool allowing you to quickly view and drill-down into Gross Margins and Sales by Category, Salesperson, and/or Region. (requires Microsoft Power BI license)  

This is available exclusively for our cloud customers as part of their subscription.  Learn more about Windward Intelligence by clicking here.

Try out Windward Business
Management Software for yourself!

No credit card required.

Request a Live Demo

Want to know more?

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1 (250) 492-8888

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